U.S. patent number 9,282,740 [Application Number 14/516,855] was granted by the patent office on 2016-03-15 for synergistic pesticidal compositions and related methods.
This patent grant is currently assigned to Dow AgroSciences LLC. The grantee listed for this patent is Dow AgroSciences LLC. Invention is credited to Luis E. Gomez, John Herbert, Ricky Hunter, Mary E. Kubiszak, Mike Shaw, Tony K. Trullinger.
United States Patent |
9,282,740 |
Gomez , et al. |
March 15, 2016 |
Synergistic pesticidal compositions and related methods
Abstract
A pesticidal composition comprises a synergistically effective
amount of a ryanodine receptor modulator compound and a pesticide
selected from N-(3-chloro-1-(pyridin-3-yl)
-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide
(I), N-(3-chloro-1
-(pyridine-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(((3,3,3-trifluoropropyl)sulf-
inyl)propanamide (II), or any agriculturally acceptable salt
thereof. A method of controlling pests comprises applying the
pesticidal composition near a population of pests. A method of
protecting a plant from infestation and attack by insects comprises
contacting the plant with the synergistic pesticidal composition.
##STR00001##
Inventors: |
Gomez; Luis E. (Carmel, IN),
Hunter; Ricky (Westfield, IN), Shaw; Mike (Carmel,
IN), Trullinger; Tony K. (Westfield, IN), Kubiszak; Mary
E. (Thorntown, IN), Herbert; John (Fishers, IN) |
Applicant: |
Name |
City |
State |
Country |
Type |
Dow AgroSciences LLC |
Indianapolis |
IN |
US |
|
|
Assignee: |
Dow AgroSciences LLC
(Indianapolis, IN)
|
Family
ID: |
52826663 |
Appl.
No.: |
14/516,855 |
Filed: |
October 17, 2014 |
Prior Publication Data
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Document
Identifier |
Publication Date |
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US 20150111736 A1 |
Apr 23, 2015 |
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Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
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61894016 |
Oct 22, 2013 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N
41/02 (20130101); A01N 43/56 (20130101); A01N
43/56 (20130101); A01N 41/10 (20130101); A01N
43/56 (20130101) |
Current International
Class: |
A01N
43/56 (20060101); A01N 41/10 (20060101) |
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Other References
PCT International Search Report; PCT/US2014/060993; dated Feb. 2,
2015. cited by applicant .
PCT Written Opinion; PCT/US2014/060993; dated Feb. 2, 2015. cited
by applicant.
|
Primary Examiner: Pak; John
Attorney, Agent or Firm: Corvin; Carl D. Traskbritt,
P.C.
Parent Case Text
CROSS-REFERENCE TO RELATED APPLICATION
This application claims the benefit of the filing of U.S.
Provisional Patent Application Ser. No. 61/894,016, filed Oct. 22,
2013, for "SYNERGISTIC PESTICIDAL COMPOSITIONS AND RELATED
METHODS," pending, the disclosure of which is hereby incorporated
herein in its entirety by this reference.
Claims
We claim:
1. A pesticidal composition comprising a synergistically effective
amount of: a ryanodine receptor modulator compound selected from
the group consisting of chlorantraniliprole, cyantraniliprole,
cyclaniliprole, flubendiamide, and mixtures thereof; and a
pesticide selected from the group consisting of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)
-N-ethyl-3-((3,3,3-trifluoropropyl)sulfinyl)propanamide (II), and
any agriculturally acceptable salt thereof ##STR00006## wherein a
weight ratio of the pesticide selected from the group consisting of
(I), (II), and any agriculturally acceptable salt thereof to the
ryanodine receptor modulator compound is greater than 1.
2. The composition of claim 1, wherein the ryanodine receptor
modulator compound is selected from the group consisting of
chlorantraniliprole, cyantraniliprole, and a mixture thereof.
3. The composition of claim 1, further comprising a
phytologically-acceptable inert carrier.
4. The composition of claim 1, further comprising an additive
selected from the group consisting of a surfactant, a stabilizer,
an emetic agent, a disintegrating agent, an antifoaming agent, a
wetting agent, a dispersing agent, a binding agent, dye, filler,
and combinations thereof.
5. The composition of claim 1, further comprising one or more
compounds having acaricidal, algicidal, avicidal, bactericidal,
fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal,
rodenticidal, virucidal or combinations thereof properties.
6. The composition of claim 1, further comprising one or more
compounds that are antifeedants, bird repellents, chemosterilants,
herbicide safeners, insect attractants, insect repellents, mammal
repellents, mating disrupters, plant activators, plant growth
regulators, synergists, or combinations thereof.
7. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 256:1.
8. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 72:1.
9. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 32:1.
10. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 16:1.
11. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 8:1.
12. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 6:1.
13. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 4:1.
14. The composition of claim 1, wherein a weight ratio of the
pesticide selected from the group consisting of (I), (II) and any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound is no more than 2:1.
15. The composition of claim 1, wherein the weight ratio of the
pesticide (I), (II), or any agriculturally acceptable salt thereof
and the ryanodine receptor modulator is X:Y; wherein, X is the
parts by weight of the pesticide (I), (II), or any agriculturally
acceptable salt thereof, and the numerical range is
0<X.ltoreq.20; Y is the parts by weight of the ryanodine
receptor modulator, and the numerical range is
0<Y.ltoreq.20.
16. A method of controlling pests comprising applying the
pesticidal composition of claim 1, near a population of pests, in
an amount sufficient to control the pests.
17. The method of claim 16, wherein the pests are brown stink bug
(Euschistus heros), diamond back moth (Plutella xylostella), or a
combination thereof.
18. The method of claim 16, wherein the pests include a member
selected from the group consisting of Order Lepidoptera,
Coleoptera, Diptera, Isoptera species, and combinations
thereof.
19. The method of claim 16, wherein the ryanodine receptor
modulator compound is selected from the group consisting of
chlorantraniliprole, cyantraniliprole, and a mixture thereof.
20. A method for protecting a plant from infestation and attack by
pests, the method comprising contacting the plant with the
pesticidal composition of claim 1.
21. The method of claim 20, wherein the ryanodine receptor
modulator compound is selected from the group consisting of
chlorantraniliprole, cyantraniliprole, and a mixture thereof.
Description
TECHNICAL FIELD
This disclosure relates to the field of compounds having pesticidal
utility against pests in Phyla Nematoda, Arthropoda, and/or
Mollusca, processes to produce such compounds and intermediates
used in such processes. These compounds may be used, for example,
as nematicides, acaricides, miticides, and/or molluscicides.
BACKGROUND
Controlling pest populations is essential to human health, modern
agriculture, food storage, and hygiene. There are more than ten
thousand species of pests that cause losses in agriculture and the
worldwide agricultural losses amount to billions of U.S. dollars
each year. Accordingly, there exists a continuous need for new
pesticides and for methods of producing and using such
pesticides.
The Insecticide Resistance Action Committee (IRAC) has classified
insecticides into categories based on the best available evidence
of the mode of action of such insecticides. Insecticides in the
IRAC Mode of Action Group 28 are ryanodine receptor modulators,
which target the nerve and muscles of the affected insects. The
insecticides in this class are believed to activate muscle
ryanodine receptors, leading to contraction and paralysis of the
affected insects. Examples of insecticides in this class are
diamides, such as chlorantraniliprole, cyantraniliprole,
cyclaniliprole, and flubendiamide.
Chlorantraniliprole
(3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chlor-
o-2-pyridinyl)-1H-pyrazole-5-carboxamide) is an anthranilic diamine
insecticide. It has been reported as an insecticide to control a
broad range of pests belonging to the Order Lepidoptera and some
Coleoptera, Diptera and Isoptera species.
Cyantraniliprole
(3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)car-
bonyl]phenyl]-1H-pyrazole-5-carboxamide) is an anthranilic diamine
insecticide. It is believed to have an insecticidal activity on a
broad range of Lepidoptera, Coleoptera, Diptera, and Isoptera
insects.
Although the rotational application of pesticides having different
modes of action may be adopted for good pest management practice,
this approach does not necessarily give satisfactory pest control.
Furthermore, even though combinations of pesticides have been
studied, a high synergistic action has not always been found.
DETAILED DESCRIPTION
As used herein, the term "synergistic effect" or grammatical
variations thereof means and includes a cooperative action
encountered in a combination of two or more active compounds in
which the combined activity of the two or more active compounds
exceeds the sum of the activity of each active compound alone.
The term "synergistically effective amount," as used herein, means
and includes an amount of two or more active compounds that provide
a synergistic effect defined above.
The term "pesticidally effective amount," as used herein, means and
includes an amount of active pesticide that causes an adverse
effect to the at least one pest, wherein the adverse effect may
include deviations from natural development, killing, regulation,
or the like.
As used herein, the term "control" or grammatical variations
thereof means and includes regulating the number of living pests or
regulating the number of viable eggs of the pests or both.
The term "ryanodine receptor modulator compound," as used herein,
means and includes any insecticides that are classified by the
Insecticide Resistance Action Committee (IRAC), based on the best
available evidence of the mode of action, to be within the IRAC
Mode of Action Group 28.
In one particular embodiment, a pesticidal composition comprises a
synergistically effective amount of a ryanodine receptor modulator
compound in combination with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio) propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl) sulfinyl)propanamide (II), or any agriculturally acceptable
salt thereof.
##STR00002##
It is appreciated that a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl) sulfinyl)propanamide (II), or any agriculturally acceptable
salt thereof may be oxidized to the corresponding sulfone in the
presence of oxygen.
As shown in the examples, the existence of synergistic effect is
determined using the method described in Colby S. R., "Calculating
Synergistic and Antagonistic Responses of Herbicide Combinations,"
Weeds, 1967, 15, 20-22.
Surprisingly, it has been found that the pesticidal composition of
the present disclosure has superior pest control at lower levels of
the combined concentrations of the ryanodine receptor modulator
compound and the pesticide (I), (II), or any agriculturally
acceptable salt thereof employed than that which may be achieved
when the ryanodine receptor modulator compound and the pesticide
(I), (II), or any agriculturally acceptable salt thereof are
applied alone. In other words, the synergistic pesticidal
composition is not a mere admixture of two active compounds
resulting in the aggregation of the properties of the active
compounds employed in the composition.
In some embodiments, the pesticidal compositions may comprise a
synergistically effective amount of a pesticide selected from (I),
(II), or any agriculturally acceptable salt thereof in combination
with cyantraniliprole. In other embodiments, the pesticidal
compositions may comprise a synergistically effective amount of a
pesticide selected from (I), (II), or any agriculturally acceptable
salt thereof in combination with chlorantraniliprole.
TABLE-US-00001 TABLE 1A Range of the Weight Ratio of Pesticide I or
II to Ryanodine No. Receptor Modulator Compound 1 20:1 to 1:20 2
15:1 to 1:15 3 10:1 to 1:10 4 5:1 to 1:5 5 4:1 to 1:4 6 3:1 to 1:3
7 2:1 to 1:2 8 1:1
Table 1A shows weight ratios of the pesticide (I), (II), or any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator in the synergistic pesticidal compositions. In some
embodiments, the weight ratio of the pesticide to the ryanodine
receptor modulator compound may be between about 20:1 and about
1:20. In some embodiments, the weight ratio of the pesticide to the
ryanodine receptor modulator compound may be between about 15:1 and
about 1:15. In some embodiments, the weight ratio of the pesticide
to the ryanodine receptor modulator compound may be between about
10:1 and about 1:10. In some embodiments, the weight ratio of the
pesticide to the ryanodine receptor modulator compound may be
between about 5:1 and about 1:5. In some embodiments, the weight
ratio of the pesticide to the ryanodine receptor modulator compound
may be between about 4:1 and about 1:4. In some embodiments, the
weight ratio of the pesticide to the ryanodine receptor modulator
compound may be between about 3:1 and about 1:3. In some
embodiments, the weight ratio of the pesticide to the ryanodine
receptor modulator compound may be between about 2:1 and about 1:2.
In some embodiments, the weight ratio of the pesticide to the
ryanodine receptor modulator compound may be about 1:1.
Additionally, the weight ratio limits of the pesticide to ryanodine
receptor modulator compound in the aforementioned embodiments may
be interchangeable. By way of non-limiting example, the weight
ratio of the pesticide to the ryanodine receptor modulator compound
may be between about 1:3 and about 20:1.
Weight ratios of the pesticide (I), (II), or any agriculturally
acceptable salt thereof to the ryanodine receptor modulator
envisioned to be synergistic pesticidal compositions may be
depicted as X:Y; wherein X is the parts by weight of the pesticide
(I), (II), or any agriculturally acceptable salt thereof, and Y is
the parts by weight of the ryanodine receptor modulator. The
numerical range of the parts by weight for X is 0<X.ltoreq.20
and the parts by weight for Y is 0<Y.ltoreq.20 as shown
graphically in TABLE 1B. By way of non-limiting example, the weight
ratio of the pesticide to the ryanodine receptor modulator compound
may be about 20:1.
TABLE-US-00002 TABLE 1B Ryanodine 20 X, Y X, Y Receptor 15 X, Y X,
Y X, Y Modulator 10 X, Y X, Y (Y) 5 X, Y X, Y X, Y X, Y Parts by 4
X, Y X, Y X, Y X, Y weight 3 X, Y X, Y X, Y X, Y X, Y X, Y 2 X, Y
X, Y X, Y X, Y 1 X, Y X, Y X, Y X, Y X, Y X, Y X, Y X, Y 1 2 3 4 5
10 15 20 Pesticide (I or II) (X) Parts by weight
Ranges of weight ratios of the pesticide (I), (II), or any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator envisioned to be synergistic pesticidal compositions may
be depicted as X.sub.1:Y.sub.1 to X.sub.2:Y.sub.2, wherein X and Y
are defined as above. In one particular embodiment, the range of
weight ratios may be X.sub.1:Y.sub.1 to X.sub.2:Y.sub.2, wherein
X.sub.1>Y.sub.1 and X.sub.2<Y.sub.2. By way of non-limiting
example, the range of weight ratios of the pesticide to the
ryanodine receptor modulator compound may be between about 3:1 and
about 1:3. In some embodiments, the range of weight ratios may be
X.sub.1:Y.sub.1 to X.sub.2:Y.sub.2, wherein X.sub.1>Y.sub.1 and
X.sub.2>Y.sub.2. By way of non-limiting example, the range of
weight ratios of the pesticide to the ryanodine receptor modulator
compound may be between about 15:1 and about 3:1. In further
embodiments, the range of weight ratios may be X.sub.1:Y.sub.1 to
X.sub.2:Y.sub.2, wherein X.sub.1<Y.sub.1 and X.sub.2<Y.sub.2.
By way of non-limiting example, the range of weight ratios of the
pesticide to the ryanodine receptor modulator compound may be
between about 1:3 and about 1:20.
Table 1C shows weight ratios of the pesticide (I), (II), or any
agriculturally acceptable salt thereof to the ryanodine receptor
modulator compound in the synergistic pesticidal compositions,
according to particular embodiments of the present disclosure. In
some particular embodiments, the weight ratio of the pesticide (I),
(II), or any agriculturally acceptable salt thereof to the
ryanodine receptor modulator compound may be no more than about
256:1. In further embodiments, the weight ratio of the pesticide to
the ryanodine receptor modulator compound may be no more than about
72:1. In further embodiments, the weight ratio of the pesticide to
the ryanodine receptor modulator compound may be no more than about
32:1. In further embodiments, the weight ratio of the pesticide to
the ryanodine receptor modulator compound may be no more than about
16:1. In further embodiments, the weight ratio of the pesticide to
the ryanodine receptor modulator compound may be no more than about
8:1. In further embodiments, the weight ratio of the pesticide to
the ryanodine receptor modulator compound may be no more than about
6:1. In further embodiments, the weight ratio of the pesticide to
the ryanodine receptor modulator compound may be no more than about
4:1. In yet further embodiments, the weight ratio of the pesticide
to the ryanodine receptor modulator compound may be no more than
about 2:1.
TABLE-US-00003 TABLE 1C Dose Rate Of Dose Rate of Ryanodine Weight
Ratio of Pesticide Pesticide (I or Receptor Modulator (I or II) to
Ryanodine II) (weight %) (weight %) Receptor Modulator 0.04
0.000156 .ltoreq.256:1 0.0025 0.0000347 .ltoreq.72:1 0.0025
0.0000781 .ltoreq.32:1 0.0025 0.000156 .ltoreq.16:1 0.0025
0.0003125 .ltoreq.8:1 0.000625 0.0000781 .ltoreq.8:1 0.000625
0.000104 .ltoreq.6:1 0.000625 0.000156 .ltoreq.4:1 0.000625
0.0003125 .ltoreq.2:1
The weight ratio of the pesticide (I), (II), or any agriculturally
acceptable salt thereof to the ryanodine receptor modulator
compound in the synergistic pesticidal composition may be varied
and different from those described in Table 1A, Table 1B, and Table
1C. One skilled in the art recognizes that the synergistic
effective amount of the combination of active compounds may vary
accordingly to various prevailing conditions. Non-limiting examples
of such prevailing conditions may include the type of pests, the
type of crops, the mode of application, the application timing, the
weather conditions, the soil conditions, the topographical
character, or the like. It is understood that one skilled in the
art may readily determine the synergistic effective amount of the
ryanodine receptor modulator compound and the pesticide (I), (II),
or any agriculturally acceptable salt thereof accordingly to the
prevailing conditions.
In some embodiments, the pesticidal compositions may comprise a
synergistically effective amount of cyantraniliprole in combination
with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl) propanamide (II), or any agriculturally acceptable
salt thereof.
In other embodiments, the pesticidal compositions may comprise a
synergistically effective amount of chlorantraniliprole in
combination with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro
propyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl) sulfinyl)propanamide (II), or any agriculturally acceptable
salt thereof.
In alternative embodiments, the pesticidal composition may comprise
a synergistically effective amount of a ryanodine receptor
modulator compound in combination with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N
-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)
-N-ethyl-3-((3,3,3-trifluoropropyl)sulfinyl)propanamide (II), or
any agriculturally acceptable salt thereof, and a
phytologically-acceptable inert carrier (e.g., solid carrier, or
liquid carrier).
In further embodiments, the pesticidal composition may further
comprise at least one additive selected from a surfactant, a
stabilizer, an emetic agent, a disintegrating agent, an antifoaming
agent, a wetting agent, a dispersing agent, a binding agent, dye,
filler, or combinations thereof.
In particular embodiments, each of the pesticides (a ryanodine
receptor modulator compound, and a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)
-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H
-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)sulfinyl)propanamide
(II), or any agriculturally acceptable salt thereof) may be
formulated separately as a wettable powder, emulsifiable
concentrate, aqueous or liquid flowable, suspension concentrate or
any one of the conventional formulations used for pesticides, and
then tank-mixed in the field with water or other liquid for
application as a liquid spray mixture. When desired, the separately
formulated pesticides may also be applied sequentially.
In some embodiments, the synergistic pesticidal composition may be
formulated into a more concentrated primary composition, which is
then diluted with water or other diluent before use. In such
embodiments, the synergistic pesticidal composition may further
comprise a surface active agent.
In one particular embodiment, the method of protecting a plant from
infestation and attack by insects comprises contacting the plant
with a pesticidal composition comprising a synergistically
effective amount of a ryanodine receptor modulator compound in
combination with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)
-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol
-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)sulfinyl)propanamide (II),
or any agriculturally acceptable salt thereof.
In some embodiments, the pesticidal compositions may be in the form
of solid. Non-limiting examples of the solid forms may include
powder, dust or granular formulations.
In other embodiments, the pesticidal compositions may be in the
form of liquid formulation. Examples of the liquid forms may
include, but not limited to, dispersion, suspension, emulsion or
solution in appropriate liquid carrier. In particular embodiments,
the synergistic pesticidal compositions may be in the form of
liquid dispersion, wherein the synergistic pesticidal compositions
may be dispersed in water or other agriculturally suitable liquid
carrier.
In certain embodiments, the synergistic pesticidal compositions may
be in the form of solution in an appropriate organic solvent. In
one embodiment, the spray oils, which are widely used in
agricultural chemistry, may be used as the organic solvent for the
synergistic pesticidal compositions.
In one particular embodiment, the method of controlling pests
comprises applying a pesticidal composition near a population of
pests, wherein the pesticidal composition comprises a
synergistically effective amount of a ryanodine receptor modulator
compound in combination with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N
-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)
-N-ethyl-3-((3,3,3-trifluoropropyl)sulfinyl)propanamide (II), or
any agriculturally acceptable salt thereof.
The control of pests may be achieved by applying a pesticidally
effective amount of the synergistic pesticidal compositions in form
of sprays, topical treatment, gels, seed coatings,
microcapsulations, systemic uptake, baits, eartags, boluses,
foggers, fumigants aerosols, dusts, or the like.
These disclosed pesticidal compositions may be used, for example,
as nematicides, acaricides, miticides, and/or molluscicides.
The pesticidal composition of the present disclosure may be used to
control a wide variety of insects. As a non-limiting example, in
one or more embodiments, the pesticidal composition may be used to
control one or more members of at least one of Phylum Arthropoda,
Phylum Nematoda, Subphylum Chelicerata, Subphylum Myriapoda,
Subphylum Hexapoda, Class Insecta, Class Arachnida, and Class
Symphyla. In at least some embodiments, the method of the present
disclosure may be used to control one or more members of at least
one of Class Insecta and Class Arachnida.
As a non-limiting example, in one or more embodiments, the method
of the present disclosure may be used to control one or more
members of at least one of Phylum Arthropoda, Phylum Nematoda,
Subphylum Chelicerata, Subphylum Myriapoda, Subphylum Hexapoda,
Class Insecta, Class Arachnida, and Class Symphyla. In at least
some embodiments, the method of the present disclosure may be used
to control one or more members of at least one of Class Insecta and
Class Arachnida.
In additional embodiments, the method of the present disclosure may
be used to control members of the Order Coleoptera (beetles)
including, but not limited to, Acanthoscelides spp. (weevils),
Acanthoscelides obtectus (common bean weevil), Agrilus planipennis
(emerald ash borer), Agriotes spp. (wireworms), Anoplophora
glabripennis (Asian longhorned beetle), Anthonomus spp. (weevils),
Anthonomus grandis (boll weevil), Aphidius spp., Apion spp.
(weevils), Apogonia spp. (grubs), Ataenius spretulus (Black
Turfgrass Ataenius), Atomaria linearis (pygmy mangold beetle),
Aulacophore spp., Bothynoderes punctiventris (beet root weevil),
Bruchus spp. (weevils), Bruchus pisorum (pea weevil), Cacoesia
spp., Callosobruchus maculatus (southern cow pea weevil),
Carpophilus hemipteras (dried fruit beetle), Cassida vittata,
Cerosterna spp., Cerotoma spp. (chrysomelids), Cerotoma trifurcata
(bean leaf beetle), Ceutorhynchus spp. (weevils), Ceutorhynchus
assimilis (cabbage seedpod weevil), Ceutorhynchus napi (cabbage
curculio), Chaetocnema spp. (chrysomelids), Colaspis spp. (soil
beetles), Conoderus scalaris, Conoderus stigmosus, Conotrachelus
nenuphar (plum curculio), Cotinus nitidis (Green June beetle),
Crioceris asparagi (asparagus beetle), Cryptolestes ferrugineus
(rusty grain beetle), Cryptolestes pusillus (flat grain beetle),
Cryptolestes turcicus (Turkish grain beetle), Ctenicera spp.
(wireworms), Curculio spp. (weevils), Cyclocephala spp. (grubs),
Cylindrocpturus adspersus (sunflower stem weevil), Deporaus
marginatus (mango leaf-cutting weevil), Dermestes lardarius (larder
beetle), Dermestes maculates (hide beetle), Diabrotica spp.
(chrysomelids), Epilachna varivestis (Mexican bean beetle),
Faustinus cubae, Hylobius pales (pales weevil), Hypera spp.
(weevils), Hypera postica (alfalfa weevil), Hyperdoes spp.
(Hyperodes weevil), Hypothenemus hampei (coffee berry beetle), Ips
spp. (engravers), Lasioderma serricorne (cigarette beetle),
Leptinotarsa decemlineata (Colorado potato beetle), Liogenys
fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus (rice water
weevil), Lyctus spp. (wood beetles/powder post beetles),
Maecolaspis joliveti, Megascelis spp., Melanotus communis,
Meligethes spp., Meligethes aeneus (blossom beetle), Melolontha
melolontha (common European cockchafer), Oberea brevis, Oberea
linearis, Oryctes rhinoceros (date palm beetle), Oryzaephilus
mercator (merchant grain beetle), Oryzaephilus surinamensis
(sawtoothed grain beetle), Otiorhynchus spp. (weevils), Oulema
melanopus (cereal leaf beetle), Oulema oryzae, Pantomorus spp.
(weevils), Phyllophaga spp. (May/June beetle), Phyllophaga cuyabana
(chrysomelids), Phynchites spp., Popillia japonica (Japanese
beetle), Prostephanus truncates (larger grain borer), Rhizopertha
dominica (lesser grain borer), Rhizotrogus spp. (European chafer),
Rhynchophorus spp. (weevils), Scolytus spp. (wood beetles),
Shenophorus spp. (Billbug), Sitona lineatus (pea leaf weevil),
Sitophilus spp. (grain weevils), Sitophilus granaries (granary
weevil), Sitophilus oryzae (rice weevil), Stegobium paniceum
(drugstore beetle), Tribolium spp. (flour beetles), Tribolium
castaneum (red flour beetle), Tribolium confusum (confused flour
beetle), Trogoderma variabile (warehouse beetle), and Zabrus
tenebioides.
In other embodiments, the method of the present disclosure may also
be used to control members of the Order Dermaptera (earwigs).
In additional embodiments, the method of the present disclosure may
be used to control members of the Order Dictyoptera (cockroaches)
including, but is not limited to, Blattella germanica (German
cockroach), Blatta orientalis (oriental cockroach), Parcoblatta
pennylvanica, Periplaneta americana (American cockroach),
Periplaneta australoasiae (Australian cockroach), Periplaneta
brunnea (brown cockroach), Periplaneta fuliginosa (smokybrown
cockroach), Pyncoselus suninamensis (Surinam cockroach), and
Supella longipalpa (brownbanded cockroach).
In further embodiments, the method of the present disclosure may be
used to control members of the Order Diptera (true flies)
including, but is not limited to, Aedes spp. (mosquitoes), Agromyza
frontella (alfalfa blotch leafminer), Agromyza spp. (leaf miner
flies), Anastrepha spp. (fruit flies), Anastrepha suspensa
(Caribbean fruit fly), Anopheles spp. (mosquitoes), Bactrocera spp.
(fruit flies), Bactrocera cucurbitae (melon fly), Bactrocera
dorsalis (oriental fruit fly), Ceratitis spp. (fruit flies),
Ceratitis capitata (Mediterranean fruit fly), Chrysops spp. (deer
flies), Cochliomyia spp. (screwworms), Contarinia spp. (Gall
midges), Culex spp. (mosquitoes), Dasineura spp. (gall midges),
Dasineura brassicae (cabbage gall midge), Delia spp., Delia platura
(seedcorn maggot), Drosophila spp. (vinegar flies), Fannia spp.
(filth flies), Fannia canicularis (little house fly), Fannia
scalaris (latrine fly), Gasterophilus intestinalis (horse bot fly),
Gracillia perseae, Haematobia irritans (horn fly), Hylemyia spp.
(root maggots), Hypoderma lineatum (common cattle grub), Liriomyza
spp. (leafminer flies), Liriomyza brassica (serpentine leafminer),
Liriomyza sativae (vegetable leafminer), Melophagus ovinus (sheep
ked), Musca spp. (muscid flies), Musca autumnalis (face fly), Musca
domestica (house fly), Oestrus ovis (sheep bot fly), Oscinella frit
(frit fly), Pegomyia betae (beet leafminer), Phorbia spp., Psila
rosae (carrot rust fly), Rhagoletis cerasi (cherry fruit fly),
Rhagoletis pomonella (apple maggot), Sitodiplosis mosellana (orange
wheat blossom midge), Stomoxys calcitrans (stable fly), Tabanus
spp. (horse flies), and Tipula spp. (crane flies).
In other embodiments, the method of the present disclosure may be
used to control members of the Order Hemiptera Sub-order
Heteroptera (true bugs) including, but is not limited to,
Acrosternum hilare (green stink bug), Blissus leucopterus (chinch
bug), Bragada hilaris, Calocoris norvegicus (potato mirid), Cimex
hemipterus (tropical bed bug), Cimex lectularius (bed bug),
Dagbertus fasciatus, Dichelops furcatus, Dysdercus suturellus
(cotton stainer), Edessa meditabunda, Eurygaster maura (cereal
bug), Euschistus heros, Euschistus servus (brown stink bug),
Helopeltis antonii, Helopeltis theivora (tea blight plantbug),
Lagynotomus spp. (stink bugs), Leptocorisa oratorius, Leptocorisa
varicornis, Lygus spp. (plant bugs), Lygus hesperus (western
tarnished plant bug), Lygus lineolaris (tarnished plant bug),
Maconellicoccus hirsutus, Neurocolpus longirostris, Nezara viridula
(southern green stink bug), Phytocoris spp. (plant bugs),
Phytocoris californicus, Phytocoris relativus, Piezodorus guildinii
(redbanded stink bug), Poecilocapsus lineatus (fourlined plant
bug), Psallus vaccinicola, Pseudacysta perseae, Scaptocoris
castanea, and Triatoma spp. (bloodsucking conenose bugs/kissing
bugs).
In additional embodiments, the method of the present disclosure may
be used to control members of the Order Hemiptera, Sub-orders
Auchenorrhyncha (Free-living Hemipterans) and Sternorrhyncha
(Plant-parasitic Hemipterans) (aphids, scales, whiteflies,
leaflhoppers) including, but is not limited to, Acrythosiphon pisum
(pea aphid), Adelges spp. (adelgids), Aleurodes proletella (cabbage
whitefly), Aleurodicus disperses, Aleurothrixus floccosus (woolly
whitefly), Aluacaspis spp., Amrasca bigutella bigutella, Aphrophora
spp. (leafhoppers), Aonidiella aurantii (California red scale),
Aphis spp. (aphids), Aphis gossypii (cotton aphid), Aphis pomi
(apple aphid), Aulacorthum solani (foxglove aphid), Bemisia spp.
(whiteflies), Bemisia argentifolii, Bemisia tabaci (sweetpotato
whitefly), Brachycolus noxius (Russian aphid), Brachycorynella
asparagi (asparagus aphid), Brevennia rehi, Brevicoryne brassicae
(cabbage aphid), Ceroplastes spp. (scales), Ceroplastes rubens (red
wax scale), Chionaspis spp. (scales), Chrysomphalus spp. (scales),
Chrysomphalus aonidum (Florida red scale) Coccus spp. (scales),
Coccus pseudomagnoliarum (citricola scale), Dysaphis plantaginea
(rosy apple aphid), Empoasca spp. (leafhoppers), Eriosoma lanigerum
(woolly apple aphid), Icerya purchasi (cottony cushion scale),
Idioscopus nitidulus (mango leafhopper), Laodelphax striatellus
(smaller brown planthopper), Lepidosaphes spp., Macrosiphum spp.,
Macrosiphum euphorbiae (potato aphid), Macrosiphum granarium
(English grain aphid), Macrosiphum rosae (rose aphid), Macrosteles
quadrilineatus (aster leafhopper), Mahanarva frimbiolata,
Metopolophium dirhodum (rose grain aphid), Mictis longicornis,
Myzus spp., Myzus persicae (green peach aphid), Nephotettix spp.
(leafhoppers), Nephotettix cinctipes (green leafhopper),
Nilaparvata lugens (brown planthopper), Paratrioza cockerelli
(tomato psyllid), Parlatoria pergandii (chaff scale), Parlatoria
ziziphi (ebony scale), Peregrinus maidis (corn delphacid),
Philaenus spp. (spittlebugs), Phylloxera vitifoliae (grape
phylloxera), Physokermes piceae (spruce bud scale), Planococcus
spp. (mealybugs), Planococcus citri (citrus mealybug), Planococcus
ficus (grape mealybug), Pseudococcus spp. (mealybugs), Pseudococcus
brevipes (pine apple mealybug), Quadraspidiotus perniciosus (San
Jose scale), Rhopalosiphum spp. (aphids), Rhopalosiphum maidis
(corn leaf aphid), Rhopalosiphum padi (oat bird-cherry aphid),
Saissetia spp. (scales), Saissetia oleae (black scale), Schizaphis
graminum (greenbug), Sitobion avenae (English grain aphid),
Sogatella furcifera (white-backed planthopper), Therioaphis spp.
(aphids), Toumeyella spp. (scales), Toxoptera spp. (aphids),
Trialeurodes spp. (whiteflies), Trialeurodes vaporariorum
(greenhouse whitefly), Trialeurodes abutiloneus (bandedwing
whitefly), Unaspis spp. (scales), Unaspis yanonensis (arrowhead
scale), and Zulia entreriana. In at least some embodiments, the
method of the present disclosure may be used to control Myzus
persicae.
In other embodiments, the method of the present disclosure may be
used to control members of the Order Hymenoptera (ants, wasps, and
sawflies) including, but not limited to, Acromyrrmex spp., Athalia
rosae, Atta spp. (leafcutting ants), Camponotus spp. (carpenter
ants), Diprion spp. (sawflies), Formica spp. (ants), Iridomyrmex
humilis (Argentine ant), Monomorium spp., Monomorium minumum
(little black ant), Monomorium pharaonis (Pharaoh ant), Neodiprion
spp. (sawflies), Pogonomyrmex spp. (harvester ants), Polistes spp.
(paper wasps), Solenopsis spp. (fire ants), Tapoinoma sessile
(odorous house ant), Tetranomorium spp. (pavement ants), Vespula
spp. (yellow jackets), and Xylocopa spp. (carpenter bees).
In certain embodiments, the method of the present disclosure may be
used to control members of the Order Isoptera (termites) including,
but not limited to, Coptotermes spp., Coptotermes curvignathus,
Coptotermes frenchii, Coptotermes formosanus (Formosan subterranean
termite), Cornitermes spp. (nasute termites), Cryptotermes spp.
(drywood termites), Heterotermes spp. (desert subterranean
termites), Heterotermes aureus, Kalotermes spp. (drywood termites),
Incistitermes spp. (drywood termites), Macrotermes spp. (fungus
growing termites), Marginitermes spp. (drywood termites),
Microcerotermes spp. (harvester termites), Microtermes obesi,
Procornitermes spp., Reticulitermes spp. (subterranean termites),
Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes
flavipes (eastern subterranean termite), Reticulitermes hageni,
Reticulitermes hesperus (western subterranean termite),
Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes
tibialis, Reticulitermes virginicus, Schedorhinotermes spp., and
Zootermopsis spp. (rotten-wood termites).
In additional embodiments, the method of the present disclosure may
be used to control members of the Order Lepidoptera (moths and
butterflies) including, but not limited to, Achoea janata,
Adoxophyes spp., Adoxophyes orana, Agrotis spp. (cutworms), Agrotis
ipsilon (black cutworm), Alabama argillacea (cotton leafworm),
Amorbia cuneana, Amyelosis transitella (navel orangeworm),
Anacamptodes defectaria, Anarsia lineatella (peach twig borer),
Anomis sabulifera (jute looper), Anticarsia gemmatalis (velvetbean
caterpillar), Archips argyrospila (fruittree leafroller), Archips
rosana (rose leaf roller), Argyrotaenia spp. (tortricid moths),
Argyrotaenia citrana (orange tortrix), Autographa gamma, Bonagota
cranaodes, Borbo cinnara (rice leaf folder), Bucculatrix
thurberiella (cotton leafperforator), Caloptilia spp. (leaf
miners), Capua reticulana, Carposina niponensis (peach fruit moth),
Chilo spp., Chlumetia transversa (mango shoot borer), Choristoneura
rosaceana (obliquebanded leafroller), Chrysodeixis spp.,
Cnaphalocerus medinalis (grass leafroller), Colias spp.,
Conpomorpha cramerella, Cossus cossus (carpenter moth), Crambus
spp. (Sod webworms), Cydiafunebrana (plum fruit moth), Cydia
molesta (oriental fruit moth), Cydia nignicana (pea moth), Cydia
pomonella (codling moth), Darna diducta, Diaphania spp. (stem
borers), Diatraea spp. (stalk borers), Diatraea saccharalis
(sugarcane borer), Diatraea graniosella (southwester corn borer),
Earias spp. (bollworms), Earias insulata (Egyptian bollworm),
Earias vitella (rough northern bollworm), Ecdytopopha aurantianum,
Elasmopalpus lignosellus (lesser cornstalk borer), Epiphysias
postruttana (light brown apple moth), Ephestia spp. (flour moths),
Ephestia cautella (almond moth), Ephestia elutella (tobacco moth),
Ephestia kuehniella (Mediterranean flour moth), Epimeces spp.,
Epinotia aporema, Erionota thrax (banana skipper), Eupoecilia
ambiguella (grape berry moth), Euxoa auxiliaris (army cutworm),
Feltia spp. (cutworms), Gortyna spp. (stemborers), Grapholita
molesta (oriental fruit moth), Hedylepta indicata (bean leaf
webber), Helicoverpa spp. (noctuid moths), Helicoverpa armigera
(cotton bollworm), Helicoverpa zea (bollworm/corn earworm),
Heliothis spp. (noctuid moths), Heliothis virescens (tobacco
budworm), Hellula undalis (cabbage webworm), Indarbela spp. (root
borers), Keiferia lycopersicella (tomato pinworm), Leucinodes
orbonalis (eggplant fruit borer), Leucoptera malifoliella,
Lithocollectis spp., Lobesia botrana (grape fruit moth), Loxagrotis
spp. (noctuid moths), Loxagrotis albicosta (western bean cutworm),
Lymantria dispar (gypsy moth), Lyonetia clerkella (apple leaf
miner), Mahasena corbetti (oil palm bagworm), Malacosoma spp. (tent
caterpillars), Mamestra brassicae (cabbage armyworm), Maruca
testulalis (bean pod borer), Metisa plana (bagworm), Mythimna
unipuncta (true armyworm), Neoleucinodes elegantalis (small tomato
borer), Nymphula depunctalis (rice caseworm), Operophthera brumata
(winter moth), Ostrinia nubilalis (European corn borer), Oxydia
vesulia, Pandemis cerasana (common currant tortrix), Pandemis
heparana (brown apple tortrix), Papilio demodocus, Pectinophora
gossypiella (pink bollworm), Peridroma spp. (cutworms), Peridroma
saucia (variegated cutworm), Perileucoptera coffeella (white coffee
leafminer), Phthorimaea operculella (potato tuber moth),
Phyllocnisitis citrella, Phyllonorycter spp. (leafminers), Pieris
rapae (imported cabbageworm), Plathypena scabs, Plodia
interpunctella (Indian meal moth), Plutella xylostella (diamondback
moth), Polychrosis viteana (grape berry moth), Prays endocarps,
Prays oleae (olive moth), Pseudaletia spp. (noctuid moths),
Pseudaletia unipunctata (armyworm), Pseudoplusia includens (soybean
looper), Rachiplusia nu, Scirpophaga incertulas, Sesamia spp.
(stemborers), Sesamia inferens (pink rice stem borer), Sesamia
nonagrioides, Setora nitens, Sitotroga cerealella (Angoumois grain
moth), Sparganothis pilleriana, Spodoptera spp. (armyworms),
Spodoptera exigua (beet armyworm), Spodoptera fugiperda (fall
armyworm), Spodoptera oridania (southern armyworm), Synanthedon
spp. (root borers), Thecla basilides, Thermisia gemmatalis, Tineola
bisselliella (webbing clothes moth), Trichoplusia ni (cabbage
looper), Tuta absoluta, Yponomeuta spp., Zeuzera coffeae (red
branch borer), and Zeuzera pyrina (leopard moth). In at least some
embodiments, the method of the present disclosure may be used to
control Spodoptera exigua.
The method of the present disclosure may be used to also control
members of the Order Mallophaga (chewing lice) including, but not
limited to, Bovicola ovis (sheep biting louse), Menacanthus
stramineus (chicken body louse), and Menopon gallinea (common hen
louse).
In additional embodiments, the method of the present disclosure may
be used to control members of the Order Orthoptera (grasshoppers,
locusts, and crickets) including, but not limited to, Anabrus
simplex (Mormon cricket), Gryllotalpidae (mole crickets), Locusta
migratoria, Melanoplus spp. (grasshoppers), Microcentrum retinerve
(angularwinged katydid), Pterophylla spp. (kaydids), chistocerca
gregaria, Scudderia furcata (forktailed bush katydid), and Valanga
nigricorni.
In other embodiments, the method of the present disclosure may be
used to control members of the Order Phthiraptera (sucking lice)
including, but not limited to, Haematopinus spp. (cattle and hog
lice), Linognathus ovillus (sheep louse), Pediculus humanus capitis
(human body louse), Pediculus humanus humanus (human body lice),
and Pthirus pubis (crab louse).
In particular embodiments, the method of the present disclosure may
be used to control members of the Order Siphonaptera (fleas)
including, but not limited to, Ctenocephalides canis (dog flea),
Ctenocephalides felis (cat flea), and Pulex irritans (human
flea).
In additional embodiments, the method of the present disclosure may
be used to control members of the Order Thysanoptera (thrips)
including, but not limited to, Caliothrips fasciatus (bean thrips),
Caliothrips phaseoli, Frankliniella fusca (tobacco thrips),
Frankliniella occidentalis (western flower thrips), Frankliniella
shultzei, Frankliniella williamsi (corn thrips), Heliothfips
haemorrhaidalis (greenhouse thrips), Riphiphorothrips cruentatus,
Scirtothrips spp., Scirtothrips citri (citrus thrips), Scirtothrips
dorsalis (yellow tea thrips), Taeniothrips rhopalantennalis, Thrips
spp., Thrips tabaci (onion thrips), and Thrips hawaiiensis
(Hawaiian flower thrips).
The method of the present disclosure may be used to also control
members of the Order Thysanura (bristletails) including, but not
limited to, Lepisma spp. (silverfish) and Thermobia spp.
(firebrats).
In further embodiments, the method of the present disclosure may be
used to control members of the Order Acari (mites and ticks)
including, but not limited to, Acarapsis woodi (tracheal mite of
honeybees), Acarus spp. (food mites), Acarus siro (grain mite),
Aceria mangiferae (mango bud mite), Aculops spp., Aculops
lycopersici (tomato russet mite), Aculops pelekasi, Aculus
pelekassi, Aculus schlechtendali (apple rust mite), Amblyomma
americanum (lone star tick), Boophilus spp. (ticks), Brevipalpus
obovatus (privet mite), Brevipalpus phoenicis (red and black flat
mite), Demodex spp. (mange mites), Dermacentor spp. (hard ticks),
Dermacentor variabilis (american dog tick), Dermatophagoides
pteronyssinus (house dust mite), Eotetranycus spp., Eotetranychus
carpini (yellow spider mite), Epitimerus spp., Eriophyes spp.,
Ixodes spp. (ticks), Metatetranycus spp., Notoedres cati,
Oligonychus spp., Oligonychus coffee, Oligonychus ilicus (southern
red mite), Panonychus spp., Panonychus citri (citrus red mite),
Panonychus ulmi (European red mite), Phyllocoptruta oleivora
(citrus rust mite), Polyphagotarsonemun latus (broad mite),
Rhipicephalus sanguineus (brown dog tick), Rhizoglyphus spp. (bulb
mites), Sarcoptes scabiei (itch mite), Tegolophus perseaflorae,
Tetranychus spp., Tetranychus urticae (twospotted spider mite), and
Varroa destructor (honey bee mite).
In additional embodiments, the method of the present disclosure may
be used to control members of the Order Nematoda (nematodes)
including, but not limited to, Aphelenchoides spp. (foliar
nematodes), Belonolaimus spp. (sting nematodes), Criconemella spp.
(ring nematodes), Dirofilaria immitis (dog heartworm), Ditylenchus
spp. (stem and bulb nematodes), Heterodera spp. (cyst nematodes),
Heterodera zeae (corn cyst nematode), Hirschmanniella spp. (root
nematodes), Hoplolaimus spp. (lance nematodes), Meloidogyne spp.
(root knot nematodes), Meloidogyne incognita (root knot nematode),
Onchocerca volvulus (hook-tail worm), Pratylenchus spp. (lesion
nematodes), Radopholus spp. (burrowing nematodes), and Rotylenchus
reniformis (kidney-shaped nematode).
In at least some embodiments, the method of the present disclosure
may be used to control at least one insect in one or more of the
Orders Lepidoptera, Coleoptera, Hemiptera, Thysanoptera, Isoptera,
Orthoptera, Diptera, Hymenoptera, and Siphonaptera, and at least
one mite in the Order Acari.
In some embodiments, the method of controlling an insect may
comprise applying a pesticidal composition near a population of
insects, wherein the pesticidal composition comprises a
synergistically effective amount of a ryanodine receptor modulator
compound in combination with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)
-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H
-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)sulfinyl)propanamide
(II), or any agriculturally acceptable salt thereof, and wherein
the insect is selected from a sap feeding brown stink bug,
Euschistus servus (Say), a lepidopteran diamond back moth, Plutella
xylostella (Linnaeus), and a combination thereof.
In one embodiment, the method of controlling an insect may comprise
applying a pesticidal composition near a population of insects,
wherein the pesticidal composition comprises a synergistically
effective amount of cyantraniliprole in combination with a
pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl) propanamide (II), or any agriculturally acceptable
salt thereof, and wherein the insect is selected from a sap feeding
brown stink bug, Euschistus servus (Say), a lepidopteran diamond
back moth, Plutella xylostella (Linnaeus), and a combination
thereof.
In another embodiment, the method of controlling an insect may
comprise applying a pesticidal composition near a population of
insects, wherein the pesticidal composition comprises a
synergistically effective amount of chlorantraniliprole in
combination with a pesticide selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio) propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl) sulfinyl)propanamide (II), or any agriculturally acceptable
salt thereof, and wherein the insect is selected from a sap feeding
brown stink bug, Euschistus servus (Say), a lepidopteran diamond
back moth, Plutella xylostella (Linnaeus), and a combination
thereof.
In a particular embodiment of the present disclosure, the
pesticidal composition may be used in conjunction (such as, in a
compositional mixture, or a simultaneous or sequential application)
with one or more compounds having acaricidal, algicidal, avicidal,
bactericidal, fungicidal, herbicidal, insecticidal, molluscicidal,
nematicidal, rodenticidal, and/or virucidal properties.
In certain embodiments of the present disclosure, the pesticidal
composition may be used in conjunction (such as, in a compositional
mixture, or a simultaneous or sequential application) with one or
more compounds that are antifeedants, bird repellents,
chemosterilants, herbicide safeners, insect attractants, insect
repellents, mammal repellents, mating disrupters, plant activators,
plant growth regulators, and/or synergists.
The pesticidal compositions of the present disclosure show a
synergistic effect, providing superior pest control at lower
pesticidally effective amounts of the combined active compounds
than when a ryanodine receptor modulator compound or a pesticide
selected from
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3
trifluoropropyl)thio)propanamide (I),
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl) sulfinyl)propanamide (II), or any agriculturally acceptable
salt thereof is used alone.
The pesticidal compositions of the present disclosure may have high
synergistic pest control and allow for a lower effective dosage
rate, an increased environmental safety, and a reduced incidence of
pest resistance.
The following examples serve to explain embodiments of the present
invention in more detail. These examples should not be construed as
being exhaustive or exclusive as to the scope of this
disclosure.
EXAMPLES
Example 1
Preparation of 3-((3,3,3-trifluoropropyl)thio)propanoyl
chloride
##STR00003##
A dry five-liter round bottom flask equipped with magnetic stirrer,
nitrogen inlet, reflux condenser, and thermometer, was charged with
3-((3,3,3-trifluoropropyl)thio)propanoic acid (prepared as
described in the PCT Publication No. WO 2013/062981 to Niyaz et
al.) (188 g, 883 mmol) in dichloromethane (CH.sub.2Cl.sub.2) (3 L).
Thionyl chloride (525 g, 321 Ml, 4.42 mol) was added dropwise over
50 minutes. The reaction mixture was heated to reflux (about
36.degree. C.) for two hours, then cooled to room temperature
(about 22.degree. C.). The resulting mixture was concentrated under
vacuum on a rotary evaporator, followed by distillation (40 Ton,
product collected at a temperature of from about 123.degree. C. to
about 127.degree. C.) to provide the title compound as a clear
colorless liquid (177.3 g, 86%): .sup.1H NMR (400 MHz, CDCl.sub.3)
.delta. 3.20 (t, J=7.1 Hz, 2H), 2.86 (t, J=7.1 Hz, 2H), 2.78-2.67
(m, 2H), 2.48-2.31 (m, 2H); .sup.19F NMR (376 MHz, CDCl.sub.3)
.delta. -66.42, -66.43, -66.44, -66.44.
Example 2
Preparation of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I)
##STR00004##
To a solution of
3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (prepared as
described in the U.S. Publication No. 2012/0110702 to Yap et al.)
(10.0 g, 44.9 mmol) in CH.sub.2Cl.sub.2 (100 mL), at a temperature
of about 0.degree. C. and under N.sub.2, was added pyridine (5.45
mL, 67.4 mmol), 4-dimethylaminopyridine (DMAP) (2.74 g, 22.45
mmol), and 3-((3,3,3-trifluoropropyl)thio)propanoyl chloride (9.91
g, 44.9 mmol), sequentially. The reaction was warmed to room
temperature and stirred for one hour. The reaction mixture was
poured into water (100 mL), and the resulting mixture was stirred
for five minutes. The mixture was transferred to a separatory
funnel, and the layers were separated. The aqueous phase was
extracted with CH.sub.2Cl.sub.2 (3.times.50 mL), and the combined
organic extracts were dried over sodium sulfate (Na.sub.2SO.sub.4),
filtered, and concentrated in vacuo. The crude product was purified
via normal phase flash chromatography (0% to 100%
EtOAc/CH.sub.2Cl.sub.2) to provide the desired product as a pale
yellow solid (17.21 g, 89%): IR (thin film) 1659 cm.sup.-1; .sup.1H
NMR (400 MHz, CDCl.sub.3) .delta. 8.95 (d, J=2.6 Hz, 1H), 8.63 (dd,
J=4.7, 1.3 Hz, 1H), 8.05 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.96 (s,
1H), 7.47 (dd, J=8.3, 4.8 Hz, 1H), 3.72 (q, J=7.1 Hz, 2H), 2.84 (t,
J=7.2 Hz, 2H), 2.66 (m, 2H), 237 (t, J=7.2 Hz, 2H), 2.44 (m, 2H),
1.17 (t, J=7.2 Hz, 3H); ESIMS m/z 409 ([M+2H].sup.+).
Example 3
Preparation of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl)propanamide (II)
##STR00005##
To a solution of
N-(3-chloro-1-(20yridine-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluo-
ropropyl)thio)propanamide (I) (500 mg, 1.229 mmol) in
hexafluoroisopropanol (5 mL) stirring at room temperature was added
30% hydrogen peroxide (523 mg, 4.92 mmol). The solution was stirred
at room temperature for 15 minutes. It was quenched with saturated
sodium sulfite solution and extracted with CH.sub.2Cl.sub.2. Silica
gel chromatography (0%-10% MeOH/CH.sub.2Cl.sub.2) gave the title
compound as white semi-solid (495 mg, 95%): IR (thin film) 1660
cm.sup.-1; .sup.1H NMR (400 MHz, CDCl.sub.3) .delta. 8.96 (d, J=2.4
Hz, 1H), 8.64 (dd, J=4.7, 1.4 Hz, 1H), 8.07-8.00 (m, 2H), 7.46
(ddd, J=8.3, 4.8, 0.7 Hz, 1H), 3.85-3.61 (m, 2H), 3.23-3.08 (m,
1H), 3.03-2.76 (m, 3H), 2.74-2.52 (m, 4H), 1.18 (t, J=7.2 Hz, 3H);
ESIMS m/z 423 ([M+H].sup.+).
Example 4
Determination of the Existence of Synergic Effect
The method described in Colby S. R., "Calculating Synergistic and
Antagonistic Responses of Herbicide Combinations," Weeds, 1967, 15,
20-22 was used to determine an existence of synergic effect between
the ryanodine receptor modulator compound and the pesticide (I),
(II), or any agriculturally acceptable salt thereof in the
formulated pesticidal composition. In this method, the percent
insect control of the formulated pesticidal composition as observed
in the study was compared to the "expected" percent control (E) as
calculated by equation (1) (hereinafter "Colby's equation")
below:
##EQU00001## where X is the percentage of control with the first
pesticide at a given rate (p), Y is the percentage of control with
the second pesticide at a given rate (q), and E is the expected
control by the first and second pesticide at a rate of p+q.
If the observed percent control of the formulated pesticidal is
greater than E, there is a synergistic effect between the ryanodine
receptor modulator compound and the pesticide (I), (II), or any
agriculturally acceptable salt thereof in the formulated pesticidal
composition. If the observed percent control of the formulated
pesticidal is equaled to or less than E, there is no synergistic
effect between the ryanodine receptor modulator compound and the
pesticide (I), (II), or any agriculturally acceptable salt thereof
in the formulated pesticidal composition.
Example 5
Synergistic Effect of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl)propanamide (II) and Cyantraniliprole Against Brown
Stink Bug, Euschistus heros
A pesticidal composition was prepared by thoroughly mixing about
0.04 weight % of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl) propanamide (hereinafter "compound II") with about
0.000156 weight % of cyantraniliprole.
Bioassays were performed wherein different active compounds were
applied to the diet of five second-instar nymphs of brown stink
bug, Euschistus heros. The percent control determined six days
after the diet treatment were as shown in TABLE 2. The percent
control of the pesticidal composition against brown stink bug,
Euschistus heros, was determined as the "Observed" action, and
compared to those obtained by using about 0.04 weight % of compound
II, and using about 0.000156 weight % of cyantraniliprole alone.
The "Colby's Expected Action" was calculated using Colby's equation
as discussed previously.
TABLE-US-00004 TABLE 2 % Control Treatment for Dose Rate Six Days
Brown Stink Bug (weight %) After Treatment Compound II 0.04 0%
Cyantraniliprole 0.000156 7% Compound II (+) 0.04 + 0.000156 25%
Cyantraniliprole Observed Action Compound II (+) 0.04 + 0.000156 7%
Cyantraniliprole Colby's Expected Action Compound II (+) 0.04 +
0.000156 18% Cyantraniliprole Differences: Observed vs.
Expected
As shown in table 2, the observed percent control of the pesticidal
composition against brown stink bug (25%) was almost four times
higher than the expected percentage control according to Colby's
equation (7%). It was surprising and unexpected that not only there
was synergistic effect between compound II and cyantraniliprole in
the pesticidal composition against brown stink bug, but also the
large magnitude of such synergistic effect. The pesticidal
composition showed 257% improvement over the Colby's expected
action against brown stink bug.
Example 6
Synergistic Effect of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl)propanamide (II) and Chlorantraniliprole Against
Diamondback Moth, Plutella xylostella
Example 6A
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound II with about 0.0003125 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds. Cabbage
plants with about two to three new-growth-true leaf stage were
treated with different pesticides using a track sprayer application
at 400 L/Ha spray volume. Three second instar diamondback moths,
Plutella xylostella, were infested onto each leaf disc. The percent
control determined after three days of the treatment were as shown
in table 3.
TABLE-US-00005 TABLE 3 % Control Treatment for Dose Rate Three Days
Diamondback Moth (weight %) After Treatment Compound II 0.0025
16.67% Chlorantraniliprole 0.0003125 66.67% Compound II (+) 0.0025
+ 0.0003125 87.5% Chlorantraniliprole Observed Action Compound II
(+) 0.0025 + 0.0003125 72.2% Chlorantraniliprole Colby's Expected
Action Compound II (+) 0.0025 + 0.0003125 15.3% Chlorantraniliprole
Differences: Observed vs. Expected
As shown in table 3, the observed percent control of the pesticidal
composition against diamondback moth (87.5%) was higher than the
expected percentage control according to Colby's equation (72.2%).
This was 21% improvement over the Colby's expected action.
Therefore, the pesticidal composition comprising 0.0025 weight % of
compound II and about 0.0003125 weight % of chlorantraniliprole
showed synergistic effect against diamondback moth.
Example 6B
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound II with about 0.0000347 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
Example 6A. The percent control determined three days after
treatment were as shown in table 4.
As shown in table 4, the observed percent control of the pesticidal
composition against diamondback moth (50%) was higher than the
expected percentage control according to Colby's equation (37.5%).
This was 33% improvement over the Colby's expected action.
Therefore, the pesticidal composition comprising 0.0025 weight % of
compound II and about 0.0000347 weight % of chlorantraniliprole
showed synergistic effect against diamondback moth.
TABLE-US-00006 TABLE 4 % Control Treatment for Dose Rate Three Days
Diamondback Moth (weight %) After Treatment Compound II 0.0025
16.67% Chlorantraniliprole 0.0000347 .sup. 25% Compound II (+)
0.0025 + 0.0000347 .sup. 50% Chlorantraniliprole Observed Action
Compound II (+) 0.0025 + 0.0000347 37.5% Chlorantraniliprole
Colby's Expected Action Compound II (+) 0.0025 + 0.0000347 12.5%
Chlorantraniliprole Differences: Observed vs. Expected
Example 6C
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound II with about 0.000156 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 5.
TABLE-US-00007 TABLE 5 % Control Treatment for Dose Rate Three Days
Diamondback Moth (weight %) After Treatment Compound II 0.0025 0%
Chlorantraniliprole 0.000156 12.5% Compound II (+) 0.0025 +
0.000156 79.17% Chlorantraniliprole Observed Action Compound II (+)
0.0025 + 0.000156 12.5% Chlorantraniliprole Colby's Expected Action
Compound II (+) 0.0025 + 0.000156 66.7% Chlorantraniliprole
Differences: Observed vs. Expected
As shown in table 5, the observed percent control of the pesticidal
composition against diamondback moth (79.17%) was significantly
higher than the expected percentage control according to Colby's
equation (12.5%). This was 533% improvement over the Colby's
expected action. Therefore, the pesticidal composition comprising
0.0025 weight % of compound II and about 0.000156 weight % of
chlorantraniliprole showed synergistic effect against diamondback
moth.
Example 6D
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound II with about 0.0000781 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 6.
TABLE-US-00008 TABLE 6 % Control Treatment for Dose Rate Three Days
Diamondback Moth (weight %) After Treatment Compound II 0.0025 0%
Chlorantraniliprole 0.0000781 4.17% Compound II (+) 0.0025 +
0.0000781 41.67% Chlorantraniliprole Observed Action Compound II
(+) 0.0025 + 0.0000781 4.2% Chlorantraniliprole Colby's Expected
Action Compound II (+) 0.0025 + 0.0000781 37.5% Chlorantraniliprole
Differences: Observed vs. Expected
As shown in table 6, the observed percent control of the pesticidal
composition against diamondback moth (41.67%) was significantly
higher than the expected percentage control according to Colby's
equation (4.2%). This was 892% improvement over the Colby's
expected action. Therefore, the pesticidal composition comprising
0.0025 weight % of compound II and about 0.0000781 weight % of
chlorantraniliprole showed synergistic effect against diamondback
moth.
Example 6E
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound II with about 0.000104 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 7.
TABLE-US-00009 TABLE 7 % Control Treatment for Dose Rate Three Days
Diamondback Moth (weight %) After Treatment Compound II 0.000625
16.67% Chlorantraniliprole 0.000104 62.5% Compound II (+) 0.000625
+ 0.000104 95.83% Chlorantraniliprole Observed Action Compound II
(+) 0.000625 + 0.000104 68.8% Chlorantraniliprole Colby's Expected
Action Compound II (+) 0.000625 + 0.000104 27.1%
Chlorantraniliprole Differ- ences: Observed vs. Expected
As shown in table 7, the observed percent control of the pesticidal
composition against diamondback moth (95.83%) was higher than the
expected percentage control according to Colby's equation (68.8%).
This was 39% improvement over the Colby's expected action.
Therefore, the pesticidal composition comprising 0.000625 weight %
of compound II and about 0.000104 weight % of chlorantraniliprole
showed synergistic effect against diamondback moth.
Example 6F
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound II with about 0.000156 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 8.
As shown in table 8, the observed percent control of the pesticidal
composition against diamondback moth (66.67%) was substantially
higher than the expected percentage control according to Colby's
equation (16.1%). This was 314% improvement over the Colby's
expected action. Therefore, the pesticidal composition comprising
0.000625 weight % of compound II and about 0.000156 weight % of
chlorantraniliprole showed synergistic effect against diamondback
moth.
TABLE-US-00010 TABLE 8 % Control Treatment for Dose Rate Three Days
Diamondback Moth (weight %) After Treatment Compound II 0.000625
4.17% Chlorantraniliprole 0.000156 12.5% Compound II (+) 0.000625 +
0.000156 66.67% Chlorantraniliprole Observed Action Compound II (+)
0.000625 + 0.000156 16.1% Chlorantraniliprole Colby's Expected
Action Compound II (+) 0.000625 + 0.000156 50.5%
Chlorantraniliprole Differ- ences: Observed vs. Expected
Example 6G
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound II with about 0.0000781 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 9.
As shown in table 9, the observed percent control of the pesticidal
composition against diamondback moth (50%) was substantially higher
than the expected percentage control according to Colby's equation
(8.2%). This was 510% improvement over the Colby's expected action.
Therefore, the pesticidal composition comprising 0.000625 weight %
of compound II and about 0.0000781 weight % of chlorantraniliprole
showed synergistic effect against diamondback moth.
TABLE-US-00011 TABLE 9 % Control Treatment for Dose Rate Three Days
Diamondback Moth (weight %) After Treatment Compound II 0.000625
4.17% Chlorantraniliprole 0.0000781 4.17% Compound II (+) 0.000625
+ 0.0000781 .sup. 50% Chlorantraniliprole Observed Action Compound
II (+) 0.000625 + 0.0000781 8.2% Chlorantraniliprole Colby's
Expected Action Compound II (+) 0.000625 + 0.0000781 41.8%
Chlorantraniliprole Differ- ences: Observed vs. Expected
Example 7
Synergistic Effect of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl)propanamide (II) and Cyantraniliprole Against
Diamondback Moth, Plutella xylostella
Example 7A
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound II with about 0.0003125 weight % of
cyantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 10.
As shown in table 10, the observed percent control of the
pesticidal composition against diamondback moth (79.17%) was
substantially higher than the expected percentage control according
to Colby's equation (29.2%). This was 171% improvement over the
Colby's expected action. Therefore, the pesticidal composition
comprising 0.0025 weight % of compound II and about 0.0003125
weight % of cyantraniliprole showed synergistic effect against
diamondback moth.
TABLE-US-00012 TABLE 10 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound II 0.0025
0% Cyantraniliprole 0.0003125 29.17% Compound II (+) 0.0025 +
0.0003125 79.17% Cyantraniliprole Observed Action Compound II (+)
0.0025 + 0.0003125 29.2% Cyantraniliprole Colby's Expected Action
Compound II (+) 0.0025 + 0.0003125 50.0% Cyantraniliprole
Differences: Observed vs. Expected
Example 7B
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound II with about 0.000156 weight % of
cyantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 11.
TABLE-US-00013 TABLE 11 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound II 0.0025
0% Cyantraniliprole 0.000156 25% Compound II (+) 0.0025 + 0.000156
70.83% Cyantraniliprole Observed Action Compound II (+) 0.0025 +
0.000156 25% Cyantraniliprole Colby's Expected Action Compound II
(+) 0.0025 + 0.000156 45.8%.sup. Cyantraniliprole Differences:
Observed vs. Expected
As shown in table 11, the observed percent control of the
pesticidal composition against diamondback moth (70.83%) was
substantially higher than the expected percentage control according
to Colby's equation (25%). This was 183% improvement over the
Colby's expected action. Therefore, the pesticidal composition
comprising 0.0025 weight % of compound II and about 0.000156 weight
% of cyantraniliprole showed synergistic effect against diamondback
moth.
Example 7C
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound II with about 0.0000781 weight % of
cyantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 12.
TABLE-US-00014 TABLE 12 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound II 0.0025
0% Cyantraniliprole 0.0000781 25% Compound II (+) 0.0025 +
0.0000781 66.67% Cyantraniliprole Observed Action Compound II (+)
0.0025 + 0.0000781 25% Cyantraniliprole Colby's Expected Action
Compound II (+) 0.0025 + 0.0000781 41.7%.sup. Cyantraniliprole
Differences: Observed vs. Expected
As shown in table 12, the observed percent control of the
pesticidal composition against diamondback moth (66.67%) was higher
than the expected percentage control according to Colby's equation
(25%). This was 167% improvement over the Colby's expected action.
Therefore, the pesticidal composition comprising 0.0025 weight % of
compound II and about 0.0000781 weight % of cyantraniliprole showed
synergistic effect against diamondback moth.
Example 7D
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound II with about 0.0003125 weight % of
cyantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth using the same procedure as that described for
example 6A. The percent control determined three days after
treatment were as shown in table 13.
TABLE-US-00015 TABLE 13 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound II
0.000625 4.17% Cyantraniliprole 0.0003125 29.17% Compound II (+)
0.000625 + 0.0003125 100% Cyantraniliprole Observed Action Compound
II (+) 0.000625 + 0.0003125 32.1% Cyantraniliprole Colby's Expected
Action Compound II (+) 0.000625 + 0.0003125 67.9% Cyantraniliprole
Differences: Observed vs. Expected
As shown in table 13, the observed percent control of the
pesticidal composition against diamondback moth (100%) was higher
than the expected percentage control according to Colby's equation
(32.1%). This was 212% improvement over the Colby's expected
action. Therefore, the pesticidal composition comprising 0.000625
weight % of compound II and about 0.0003125 weight % of
cyantraniliprole showed synergistic effect against diamondback
moth.
Example 8
Synergistic Effect of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I) and Chlorantraniliprole Against
Diamondback Moth, Plutella xylostella
Example 8A
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (hereinafter "compound I") with about
0.0000781 weight % of chlorantraniliprole.
Bioassays were performed for different active compounds. Cabbage
plants with about two to three new-growth-true leaf stage were
treated with different pesticides using a track sprayer at a rate
of 400 L/Ha. Three second instar diamondback moths, Plutella
xylostella, were infested onto each leaf disc. The percent control
determined three days after treatment were as shown in table
14.
TABLE-US-00016 TABLE 14 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound I 0.0025
4.35% Chlorantraniliprole 0.0000781 30.43% Compound I (+) 0.0025 +
0.0000781 82.61% Chlorantraniliprole Observed Action Compound I (+)
0.0025 + 0.0000781 33.46% Chlorantraniliprole Colby's Expected
Action Compound I (+) 0.0025 + 0.0000781 49.51% Chlorantraniliprole
Differences: Observed vs. Expected
As shown in table 14, the observed percent control of the
pesticidal composition against diamondback moth (82.61%) was higher
than the expected percentage control according to Colby's equation
(30.43%). This was about 147% improvement over the Colby's expected
action. Therefore, the pesticidal composition comprising 0.0025
weight % of compound I and about 0.0000781 weight % of
chlorantraniliprole showed significant synergistic effect against
diamondback moth, Plutella xylostella.
Example 8B
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound I with about 0.000156 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth, Plutella xylostella, according to the procedure
described in example 8A. The percent control determined three days
after treatment were as shown in table 15.
TABLE-US-00017 TABLE 15 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound I
0.000625 0% Chlorantraniliprole 0.000156 73.91% Compound I (+)
0.000625 + 0.000156 91.30% Chlorantraniliprole Observed Action
Compound I (+) 0.000625 + 0.000156 73.91% Chlorantraniliprole
Colby's Expected Action Compound I (+) 0.000625 + 0.000156 17.39%
Chlorantraniliprole Differ- ences: Observed vs. Expected
As shown in table 15, the observed percent control of the
pesticidal composition against diamondback moth (91.30%) was higher
than the expected percentage control according to Colby's equation
(73.91%). This was about 23.5% improvement over the Colby's
expected action. Therefore, the pesticidal composition comprising
0.000625 weight % of compound I and about 0.000156 weight % of
chlorantraniliprole showed synergistic effect against diamondback
moth, Plutella xylostella.
Example 8C
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound I with about 0.0000781 weight % of
chlorantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth, Plutella xylostella, according to the procedure
described in example 8A. The percent control determined three days
after treatment were as shown in table 16.
TABLE-US-00018 TABLE 16 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound I
0.000625 0% Chlorantraniliprole 0.0000781 30.43% Compound I (+)
0.000625 + 0.0000781 69.56% Chlorantraniliprole Observed Action
Compound I (+) 0.000625 + 0.0000781 30.43% Chlorantraniliprole
Colby's Expected Action Compound I (+) 0.000625 + 0.0000781 39.13%
Chlorantraniliprole Differ- ences: Observed vs. Expected
As shown in table 16, the observed percent control of the
pesticidal composition against diamondback moth (69.56%) was higher
than the expected percentage control according to Colby's equation
(30.43%). This was about 128.6% improvement over the Colby's
expected action. Therefore, the pesticidal composition comprising
0.000625 weight % of compound I and about 0.0000781 weight % of
chlorantraniliprole showed significant synergistic effect against
diamondback moth, Plutella xylostella.
Example 9
Synergistic Effect of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I) and Cyantraniliprole Against
Diamondback Moth, Plutella xylostella
Example 9A
A pesticidal composition was prepared by thoroughly mixing about
0.0025 weight % of compound I with about 0.000156 weight % of
cyantraniliprole.
Bioassays were performed for different active compounds. Cabbage
plants with about two to three new-growth-true leaf stage were
treated with different pesticides using a track sprayer at a rate
of 400 L/Ha. Three second instar diamondback moths, Plutella
xylostella, were infested onto each leaf disc. The percent control
determined three days after treatment were as shown in table
17.
TABLE-US-00019 TABLE 17 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound I 0.0025
4.35% Cyantraniliprole 0.000156 73.91% Compound I (+) 0.0025 +
0.000156 91.3% Cyantraniliprole Observed Action Compound I (+)
0.0025 + 0.000156 75.04% Cyantraniliprole Colby's Expected Action
Compound I (+) 0.0025 + 0.000156 16.26% Cyantraniliprole
Differences: Observed vs. Expected
As shown in table 17, the observed percent control of the
pesticidal composition against diamondback moth (91.3%) was higher
than the expected percentage control according to Colby's equation
(75.04%). This was about 21.67% improvement over the Colby's
expected action. Therefore, the pesticidal composition comprising
0.0025 weight % of compound II and about 0.000156 weight % of
cyantraniliprole showed synergistic effect against diamondback
moth.
Example 9B
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound I with about 0.0003125 weight % of
cyantraniliprole.
Bioassays were performed for different active compounds against
diamondback moth, Plutella xylostella, according to the procedure
described in example 9A. The percent control determined three days
after treatment were as shown in table 18.
As shown in table 18, the observed percent control of the
pesticidal composition against diamondback moth (100%) was higher
than the expected percentage control according to Colby's equation
(91.30%). This was about 9.53% improvement over the Colby's
expected action. Therefore, the pesticidal composition comprising
0.000625 weight % of compound II and about 0.0003125 weight % of
cyantraniliprole showed synergistic effect against diamondback
moth.
TABLE-US-00020 TABLE 18 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound I
0.000625 0% Cyantraniliprole 0.0003125 91.30% Compound I (+)
0.000625 + 0.0003125 .sup. 100% Cyantraniliprole Observed Action
Compound I (+) 0.000625 + 0.0003125 91.30% Cyantraniliprole Colby's
Expected Action Compound I (+) 0.000625 + 0.0003125 8.70%
Cyantraniliprole Differences: Observed vs. Expected
Example 10
Synergistic Effect of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I) and Flubendiamide Against Diamondback
Moth, Plutella xylostella
A pesticidal composition was prepared by thoroughly mixing about
0.000625 weight % of compound I with about 0.0003125 weight % of
flubendiamide.
Bioassays were performed for different active compounds against
diamondback moth, Plutella xylostella, according to the procedure
described in example 9A. The percent control determined three days
after treatment were as shown in table 19.
As shown in table 19, the observed percent control of the
pesticidal composition against diamondback moth (17.39%) was higher
than the expected percentage control according to Colby's equation
(8.70%). This was almost 100% improvement over the Colby's expected
action. Therefore, the pesticidal composition comprising 0.0025
weight % of compound I and about 0.0003125 weight % of
flubendiamide showed synergistic effect against diamondback moth,
Plutella xylostella.
TABLE-US-00021 TABLE 19 % Control Treatment for Dose Rate Three
Days Diamondback Moth (weight %) After Treatment Compound I 0.0025
0% Flubendiamide 0.0003125 8.70% Compound I (+) Flubendiamide
0.0025 + 0.0003125 17.39% Observed Action Compound I (+)
Flubendiamide 0.0025 + 0.0003125 8.70% Colby's Expected Action
Compound I (+) 0.0025 + 0.0003125 8.69% Flubendiamide Differences:
Observed vs. Expected
Prophetic Example PE-11
Synergistic Effect of
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)thio)propanamide (I) or
N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro-
propyl)sulfinyl)propanamide (II) and Cyantraniliprole,
Chlorantraniliprole, or Flubendiamide
A pesticidal composition may be prepared by thoroughly mixing
compound I (weight %) or compound II (weight %) with
cyantraniliprole, chlorantraniliprole, or flubendiamide (weight
%).
The bioassays may be performed for different active compounds
against brown stink bug, Euschistus heros, using the same procedure
as that described in example 5. The percent control may be
determined some time after treatment.
The bioassays may be performed for different active compounds
against diamondback moth, Plutella xylostella, using the same
procedure as that described for example 6A. The percent control may
be determined some time after treatment.
The observed percent control of the pesticidal composition against
brown stink bug is expected to be higher than the expected
percentage control according to Colby's equation. Therefore, the
pesticidal composition comprising compound I (weight %) or compound
II (weight %) and cyantraniliprole, chlorantraniliprole, or
flubendiamide (weight %) is expected to show synergistic effect
against brown stink bug.
The observed percent control of the pesticidal composition against
diamondback moth is expected to be higher than the expected
percentage control according to Colby's equation. Therefore, the
pesticidal composition comprising compound I (weight %) or compound
II (weight %) and cyantraniliprole, chlorantraniliprole, or
flubendiamide (weight %) is expected to show synergistic effect
against diamondback moth.
While the present disclosure may be susceptible to various
modifications and alternative forms, specific embodiments have been
described by way of example in detail herein. However, it should be
understood that the present disclosure is not intended to be
limited to the particular forms disclosed. Rather, the present
disclosure is to cover all modifications, equivalents, and
alternatives falling within the scope of the present disclosure as
defined by the following appended claims and their legal
equivalents.
* * * * *